2-Meth­oxy-4-(prop-2-en-1-yl)phenyl 2,4-di­chloro­benzoate

Pichika, M.R.; Kang, Y.B.; Ng, S.W.

doi:10.1107/S1600536813015675

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1089

https://doi.org/10.1107/S1600536813015675

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2-Methoxy-4-(prop-2-en-1-yl)phenyl 2,4-dichlorobenzoate

Mallikarjuna Rao Pichika,^a ^* Yew Beng Kang ^a and Seik Weng Ng ^b,^c

^aDepartment of Pharmaceutical Chemistry, International Medical University, 126 Jalan Bukit Jalil, 57000 Kuala Lumpur, Malaysia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: mallikarjunarao_pichika@imu.edu.my

(Received 3 June 2013; accepted 5 June 2013; online 12 June 2013)

In the title compound, C₁₇H₁₄Cl₂O₃, the two benzene rings are twisted by 73.6 (2)°. The twist is similar to that found in the unsubstituted compound, viz. phenyl benzoate. In the crystal, inversion dimers are linked by pairs of C—H⋯O interactions.

Related literature

For the structure of phenyl benzoate, see: Shibakami & Sekiya (1995 ).

Experimental

Crystal data

C₁₇H₁₄Cl₂O₃
M_r = 337.18
Triclinic, $[P \overline 1]$
a = 7.8805 (8) Å
b = 8.4673 (12) Å
c = 12.3973 (14) Å
α = 104.166 (11)°
β = 94.502 (9)°
γ = 104.145 (10)°
V = 769.29 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.847, T_max = 0.919
4945 measured reflections
2703 independent reflections
1818 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.269
S = 1.09
2703 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.95	2.52	3.339 (7)	144
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015675/bt6913sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015675/bt6913Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015675/bt6913Isup3.cml

checkCIF report

Comment top

The title phenyl benzoate (Scheme I, Fig. 1), which possesses an allyl and a methoxy substituent, was synthesized for an evaluation of its pharmaceutical properties as it is an ester derivative of eugenol. The two benzene rings are approximately perpendicular [dihedral angle 73.6 (25) °]. The twist is similar to that found in the unsubstituted compound, phenyl benzoate (Shibakami & Sekiya, 1995).

Related literature top

For the structure of phenyl benzoate, see: Shibakami & Sekiya (1995).

Experimental top

4-Allyl-2-methoxyphenol (1 mmol), 2,4-dichlorobenzoic acid (1 mmol), diethylazodicarboxylate (2 mmol) and triphenylphosphine (2 mmol) were heated in THF (10 ml) for 2 h. The solid material extracted with dichloromethane. The dichloromethane solution was eluted through a silica gel column by using an n-hexane–ethyl acetate (95: 5 v/v) solvent system. Slow evaporation of the solution yielded large colorless crystals.

Structure description top

For the structure of phenyl benzoate, see: Shibakami & Sekiya (1995).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₇H₁₄Cl₂O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-Methoxy-4-(prop-2-en-1-yl)phenyl 2,4-dichlorobenzoate top

Crystal data top

C₁₇H₁₄Cl₂O₃	Z = 2
M_r = 337.18	F(000) = 348
Triclinic, P1	D_x = 1.456 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8805 (8) Å	Cell parameters from 1164 reflections
b = 8.4673 (12) Å	θ = 3.0–25.0°
c = 12.3973 (14) Å	µ = 0.43 mm⁻¹
α = 104.166 (11)°	T = 100 K
β = 94.502 (9)°	Prism, colourless
γ = 104.145 (10)°	0.40 × 0.20 × 0.20 mm
V = 769.29 (16) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2703 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1818 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.057
Detector resolution: 10.4041 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→10
T_min = 0.847, T_max = 0.919	l = −14→9
4945 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.269	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1481P)² + 0.2039P] where P = (F_o² + 2F_c²)/3
2703 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₇H₁₄Cl₂O₃	γ = 104.145 (10)°
M_r = 337.18	V = 769.29 (16) Å³
Triclinic, P1	Z = 2
a = 7.8805 (8) Å	Mo Kα radiation
b = 8.4673 (12) Å	µ = 0.43 mm⁻¹
c = 12.3973 (14) Å	T = 100 K
α = 104.166 (11)°	0.40 × 0.20 × 0.20 mm
β = 94.502 (9)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2703 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1818 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.919	R_int = 0.057
4945 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.269	H-atom parameters constrained
S = 1.09	Δρ_max = 1.02 e Å⁻³
2703 reflections	Δρ_min = −0.64 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.61313 (17)	0.1630 (2)	0.41224 (12)	0.0305 (5)
Cl2	1.30151 (17)	0.3673 (2)	0.56261 (11)	0.0286 (5)
O1	0.5171 (5)	0.5487 (5)	0.1955 (3)	0.0248 (10)
O2	0.5571 (5)	0.2458 (5)	0.2059 (3)	0.0247 (10)
O3	0.7704 (5)	0.3027 (5)	0.0993 (3)	0.0244 (10)
C1	0.4077 (7)	0.4099 (7)	0.1176 (4)	0.0196 (12)
C2	0.2748 (7)	0.4127 (7)	0.0377 (4)	0.0210 (13)
H2	0.2580	0.5184	0.0333	0.025*
C3	0.1662 (7)	0.2644 (8)	−0.0358 (4)	0.0225 (13)
C4	0.1948 (7)	0.1095 (7)	−0.0313 (5)	0.0232 (13)
H4	0.1231	0.0072	−0.0820	0.028*
C5	0.3276 (7)	0.1049 (8)	0.0470 (5)	0.0252 (14)
H5	0.3464	−0.0005	0.0504	0.030*
C6	0.4327 (7)	0.2539 (7)	0.1202 (4)	0.0205 (13)
C7	0.4783 (8)	0.7069 (7)	0.1996 (5)	0.0297 (15)
H7A	0.5628	0.7976	0.2581	0.045*
H7B	0.3579	0.7001	0.2170	0.045*
H7C	0.4876	0.7311	0.1266	0.045*
C8	0.0147 (7)	0.2725 (8)	−0.1161 (4)	0.0258 (14)
H8A	−0.0981	0.2270	−0.0902	0.031*
H8B	0.0251	0.3927	−0.1123	0.031*
C9	0.0062 (8)	0.1778 (8)	−0.2361 (5)	0.0286 (15)
H9	0.1073	0.2072	−0.2716	0.034*
C10	−0.1295 (9)	0.0577 (8)	−0.2954 (5)	0.0335 (15)
H10A	−0.2329	0.0248	−0.2627	0.040*
H10B	−0.1250	0.0032	−0.3714	0.040*
C11	0.7283 (7)	0.2824 (7)	0.1879 (5)	0.0218 (13)
C12	0.8567 (7)	0.2914 (7)	0.2851 (4)	0.0218 (13)
C13	0.8232 (7)	0.2503 (7)	0.3850 (5)	0.0209 (13)
C14	0.9597 (7)	0.2728 (7)	0.4692 (4)	0.0216 (13)
H14	0.9352	0.2423	0.5363	0.026*
C15	1.1335 (7)	0.3406 (8)	0.4549 (4)	0.0222 (13)
C16	1.1726 (7)	0.3802 (7)	0.3571 (4)	0.0237 (13)
H16	1.2917	0.4228	0.3469	0.028*
C17	1.0337 (7)	0.3565 (8)	0.2737 (4)	0.0245 (13)
H17	1.0595	0.3855	0.2063	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0151 (8)	0.0452 (11)	0.0321 (9)	0.0026 (7)	0.0048 (6)	0.0172 (7)
Cl2	0.0183 (8)	0.0381 (10)	0.0272 (9)	0.0058 (7)	−0.0021 (6)	0.0082 (7)
O1	0.018 (2)	0.026 (2)	0.027 (2)	0.0043 (18)	−0.0019 (16)	0.0035 (18)
O2	0.019 (2)	0.034 (2)	0.023 (2)	0.0072 (18)	0.0033 (16)	0.0102 (18)
O3	0.021 (2)	0.028 (2)	0.023 (2)	0.0034 (18)	0.0032 (16)	0.0096 (18)
C1	0.016 (3)	0.017 (3)	0.020 (3)	0.000 (2)	0.003 (2)	−0.001 (2)
C2	0.019 (3)	0.029 (3)	0.017 (3)	0.008 (3)	0.003 (2)	0.006 (2)
C3	0.019 (3)	0.030 (3)	0.020 (3)	0.008 (3)	0.009 (2)	0.007 (3)
C4	0.020 (3)	0.021 (3)	0.026 (3)	0.000 (3)	0.003 (2)	0.009 (3)
C5	0.020 (3)	0.027 (3)	0.032 (3)	0.008 (3)	0.007 (2)	0.010 (3)
C6	0.016 (3)	0.026 (3)	0.019 (3)	0.006 (2)	0.002 (2)	0.006 (2)
C7	0.024 (3)	0.021 (3)	0.038 (4)	0.005 (3)	−0.001 (3)	0.000 (3)
C8	0.018 (3)	0.023 (3)	0.033 (3)	0.003 (3)	0.000 (2)	0.007 (3)
C9	0.021 (3)	0.043 (4)	0.025 (3)	0.012 (3)	0.004 (2)	0.012 (3)
C10	0.038 (4)	0.025 (4)	0.034 (4)	0.011 (3)	−0.004 (3)	0.002 (3)
C11	0.017 (3)	0.016 (3)	0.030 (3)	0.005 (2)	0.007 (2)	0.002 (3)
C12	0.018 (3)	0.022 (3)	0.023 (3)	0.008 (2)	−0.001 (2)	0.001 (2)
C13	0.012 (3)	0.021 (3)	0.029 (3)	0.004 (2)	0.002 (2)	0.006 (2)
C14	0.021 (3)	0.024 (3)	0.020 (3)	0.010 (3)	0.001 (2)	0.002 (2)
C15	0.019 (3)	0.030 (3)	0.016 (3)	0.008 (3)	0.001 (2)	0.002 (2)
C16	0.014 (3)	0.027 (3)	0.025 (3)	0.000 (2)	0.002 (2)	0.003 (3)
C17	0.027 (3)	0.031 (4)	0.016 (3)	0.008 (3)	0.005 (2)	0.006 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.736 (5)	C7—H7C	0.9800
Cl2—C15	1.736 (5)	C8—C9	1.494 (8)
O1—C1	1.369 (6)	C8—H8A	0.9900
O1—C7	1.436 (7)	C8—H8B	0.9900
O2—C11	1.357 (6)	C9—C10	1.303 (9)
O2—C6	1.414 (6)	C9—H9	0.9500
O3—C11	1.210 (7)	C10—H10A	0.9500
C1—C6	1.390 (8)	C10—H10B	0.9500
C1—C2	1.393 (7)	C11—C12	1.486 (8)
C2—C3	1.390 (8)	C12—C13	1.393 (8)
C2—H2	0.9500	C12—C17	1.401 (8)
C3—C4	1.397 (8)	C13—C14	1.382 (7)
C3—C8	1.520 (7)	C14—C15	1.393 (8)
C4—C5	1.385 (8)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.373 (8)
C5—C6	1.383 (7)	C16—C17	1.386 (8)
C5—H5	0.9500	C16—H16	0.9500
C7—H7A	0.9800	C17—H17	0.9500
C7—H7B	0.9800

C1—O1—C7	115.8 (4)	C3—C8—H8B	108.5
C11—O2—C6	115.7 (4)	H8A—C8—H8B	107.5
O1—C1—C6	116.3 (5)	C10—C9—C8	124.8 (6)
O1—C1—C2	125.6 (5)	C10—C9—H9	117.6
C6—C1—C2	118.1 (5)	C8—C9—H9	117.6
C3—C2—C1	121.5 (5)	C9—C10—H10A	120.0
C3—C2—H2	119.2	C9—C10—H10B	120.0
C1—C2—H2	119.2	H10A—C10—H10B	120.0
C2—C3—C4	119.1 (5)	O3—C11—O2	122.4 (5)
C2—C3—C8	119.7 (5)	O3—C11—C12	123.7 (5)
C4—C3—C8	121.2 (5)	O2—C11—C12	114.0 (5)
C5—C4—C3	120.0 (5)	C13—C12—C17	117.4 (5)
C5—C4—H4	120.0	C13—C12—C11	128.7 (5)
C3—C4—H4	120.0	C17—C12—C11	113.8 (5)
C6—C5—C4	119.9 (5)	C14—C13—C12	121.1 (5)
C6—C5—H5	120.0	C14—C13—Cl1	115.1 (4)
C4—C5—H5	120.0	C12—C13—Cl1	123.8 (4)
C5—C6—C1	121.4 (5)	C13—C14—C15	119.5 (5)
C5—C6—O2	119.1 (5)	C13—C14—H14	120.3
C1—C6—O2	119.3 (5)	C15—C14—H14	120.3
O1—C7—H7A	109.5	C16—C15—C14	121.3 (5)
O1—C7—H7B	109.5	C16—C15—Cl2	120.5 (4)
H7A—C7—H7B	109.5	C14—C15—Cl2	118.2 (4)
O1—C7—H7C	109.5	C15—C16—C17	118.2 (5)
H7A—C7—H7C	109.5	C15—C16—H16	120.9
H7B—C7—H7C	109.5	C17—C16—H16	120.9
C9—C8—C3	114.9 (4)	C16—C17—C12	122.4 (5)
C9—C8—H8A	108.5	C16—C17—H17	118.8
C3—C8—H8A	108.5	C12—C17—H17	118.8
C9—C8—H8B	108.5

C7—O1—C1—C6	−173.9 (5)	C6—O2—C11—O3	−7.7 (7)
C7—O1—C1—C2	5.8 (7)	C6—O2—C11—C12	173.5 (4)
O1—C1—C2—C3	−177.9 (5)	O3—C11—C12—C13	−171.3 (6)
C6—C1—C2—C3	1.7 (8)	O2—C11—C12—C13	7.5 (8)
C1—C2—C3—C4	−1.9 (8)	O3—C11—C12—C17	11.4 (8)
C1—C2—C3—C8	175.7 (5)	O2—C11—C12—C17	−169.9 (4)
C2—C3—C4—C5	1.2 (8)	C17—C12—C13—C14	−0.1 (8)
C8—C3—C4—C5	−176.3 (5)	C11—C12—C13—C14	−177.4 (5)
C3—C4—C5—C6	−0.5 (8)	C17—C12—C13—Cl1	−178.2 (4)
C4—C5—C6—C1	0.4 (8)	C11—C12—C13—Cl1	4.6 (9)
C4—C5—C6—O2	174.5 (4)	C12—C13—C14—C15	1.2 (8)
O1—C1—C6—C5	178.7 (5)	Cl1—C13—C14—C15	179.4 (4)
C2—C1—C6—C5	−1.0 (8)	C13—C14—C15—C16	−2.3 (9)
O1—C1—C6—O2	4.6 (7)	C13—C14—C15—Cl2	179.9 (4)
C2—C1—C6—O2	−175.1 (4)	C14—C15—C16—C17	2.2 (9)
C11—O2—C6—C5	103.7 (6)	Cl2—C15—C16—C17	180.0 (4)
C11—O2—C6—C1	−82.0 (6)	C15—C16—C17—C12	−1.1 (9)
C2—C3—C8—C9	130.2 (6)	C13—C12—C17—C16	0.1 (8)
C4—C3—C8—C9	−52.2 (7)	C11—C12—C17—C16	177.8 (5)
C3—C8—C9—C10	122.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.95	2.52	3.339 (7)	144
C17—H17···O3	0.95	2.39	2.746 (6)	101

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄Cl₂O₃
M_r	337.18
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.8805 (8), 8.4673 (12), 12.3973 (14)
α, β, γ (°)	104.166 (11), 94.502 (9), 104.145 (10)
V (Å³)	769.29 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.847, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	4945, 2703, 1818
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.269, 1.09
No. of reflections	2703
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.64

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.9500	2.5200	3.339 (7)	144.00
C17—H17···O3	0.9500	2.3900	2.746 (6)	101.00

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

We thank the Ministry of Higher Education, Malaysia (ERGS/1/2012/STG01/IMU/02/1; UM-C/HIR-MOHE/SC/03) for supporting this study and the International Medical University for providing the facilities.

References

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